Tours and Trips in Chicago

On a daytime helicopter tour over Chicago, enjoy views of the city's famed architecture and other sights from the air. You'll fly over Willis Tower (the old Sears Tower), Wrigley Field, Lincoln Park, and more while a pilot provides commentary about the city as you go.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city's top attractions with the CityPASS. This easy-to-carry booklet grants you free entry into top-tier sights including the Shedd Aquarium, Field Museum, Art Institute of Chicago, Adler Planetarium, Skydeck Chicago, Museum of Science and Industry and 360 Chicago (John Hancock Observatory). Plus enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.

Celebrate the holidays in style during this 90-minute excursion, featuring a trolley tour of Christmas lights at some of Chicago's most famous sights, followed by a shopping trip to the German-themed Christkindlmarket. See Lincoln Park, Daley Plaza and Michigan Avenue adorned with lights for the holiday season. Then find something for the important people on your list at the Christkindlmarket, a German-tinged Christmas offering unique gifts and fun-filled activities for the whole family.

Explore Chicago's buzzing food scene with a small group on this 3-hour walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste some classic Chicago foods!

This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.

Soak up the Windy City's festive holiday feel and explore local landmarks with ease on this 2-hour Segway tour in Chicago. Hop onto your Segway and spin through Chicago's Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive displays at Macy's department store. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city's Christmas tree. Numbers are limited to eight for a small-group experience.

Stroll through downtown Chicago on this 2.5-hour food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, brownies, and local beer. All tastings and beverages are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.

Celebrate the holidays in Chicago with a special scenic helicopter ride that provides a dazzling perspective on the Windy City's top attractions. Depart from a heliport located downtown near the Loop and fly over illuminated landmarks such as Willis Tower (formerly Sears Tower), Navy Pier, Wrigley Field, Lincoln Park Zoo, and Lake Michigan while listening to commentary from your pilot about the history of Chicago. At the heliport, you can enjoy hot chocolate and seasonal treats, history exhibits, and an interactive flight simulator.

Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah's penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.

Take a film-lover's exploration of the Windy City during this 2-hour Chicago movie tour. Whether you're a movie die-hard or just looking for a unique way to explore Chicago, this tour offers a 30 mile (48km) trip by air-conditioned coach past the locations where movies such as Ferris Bueller's Day Off, The Dark Knight and Transformers 3 were filmed. In addition to seeing the filming locations, you'll also have a chance to visit iconic Chicago neighborhoods including Lincoln Park, Wrigleyville, the Gold Coast and Old Town among others. This Chicago film tour also includes a guide.

Soar above the city lights of Chicago on a 15-minute nighttime helicopter ride with live narration by experienced pilots. Enjoy birds-eye views of downtown landmarks, then bank past Navy Pier to Lincoln Park and Uptown. Hear about the history of the city as you take in unforgettable views of downtown's bristling skyscrapers, and see Willis Tower, Millennium Park and Soldier Field. This unique experience offers a once in a lifetime view of the Second City at its most stunning.

Board a luxury yacht for a 3-hour dinner cruise on New Year's Eve in Chicago. Choose to be seated in the rooftop lounge or explore the well-appointed ship before sitting down for a 3-course, gourmet meal. Relax with tea and coffee while taking in views of the skyline or dancing to the onboard DJ.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit Chicago's 'front yard,' the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths and rose gardens of Grant Park to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city's iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city's beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain's breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Discover the 'dark side' of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine's Day Massacre, learn about 'The Enforcer's Safe,' and stop by local watering holes.

Soar above the incredible skyline of Chicago during this 15-minute helicopter flight above the Windy City. Climb aboard your high-tech helicopter for a ride like no other, admiring views of Lake Michigan plus iconic city sights like Millennium Park, Lincoln Park, Navy Pier, the Shedd Aquarium and the Willis Tower. Along the way you'll hear informative details about the various landmarks from your pilot, who will provide commentary during the flight. Tour route is subject to change.

Explore Chicago's gangster past on this 1.5-hour mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago's criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine's Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

Step into the heart of Chicago with this 2-hour walking tour of the Loop. You'll meet your local guide at the Chicago Cultural Center and make your way through the city's downtown. Stop to check out the elevated "L" train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You'll come away with a deeper sense of Chicago's rich history and architecture.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain's breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.